Stereochemical determination of chlorophyll-d molecule from Acaryochloris marina and its modification to a self-aggregative chlorophyll as a model of green photosynthetic bacterial antennae

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Tadashi MizoguchiHitoshi Tamiaki

Abstract

Acaryochloris marina is a unique photosynthetic prokaryote containing chlorophyll(Chl)-d as a major photoactive pigment (over 95%). The molecular structure of Chl-d is proposed as the 3-formyl analog of Chl-a. However, the stereochemistry of Chl-d at the 13(2)-, 17- and 18-positions has not yet been established unambiguously. In the first part of this paper, we describe the determination of their stereochemistries to be 13(2)-(R)-, 17-(S)- and 18-(S)-configurations by using 1H-1H NOE correlations in 1H-NMR and circular dichroism spectra as well as chemical modification of Chl-a to produce stereochemically defined Chl derivatives. In the second part of the paper, we report a facile synthesis of a self-aggregative Chl by modifying isolated Chl-d. Since Chl-d was characterized by its reactive 3-formyl group, the formyl group was reduced with t-BuNH2BH3 to afford the desirable Chl, 3-deformyl-3-hydroxymethyl-pyrochlorophyll-d (3(1)-OH-pyroChl-d). The synthetic 3(1)-OH-pyroChl-d molecules spontaneously self-organized to form well-ordered aggregates in a non-polar organic solvent. The self-aggregates are a good model of major light-harvesting antenna systems of green photosynthetic bacteria, chlorosomes, in terms of the following thr...Continue Reading

References

Jan 28, 1986·Biochimica Et Biophysica Acta·P D Gerola, J M Olson
Mar 27, 2003·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Tadashi MizoguchiHitoshi Tamiaki
Dec 31, 2003·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Yoshitaka SagaHitoshi Tamiaki
Mar 16, 2004·Science·Akio MurakamiMamoru Mimuro
Apr 22, 2005·Angewandte Chemie·Valerie HuberFrank Würthner
Aug 27, 2005·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Hitoshi Tamiaki

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Citations

Mar 12, 2008·Photochemistry and Photobiology·Anita ZupcanovaFrantisek Vacha
Jul 26, 2012·Photochemistry and Photobiology·Yoshitaka SagaHitoshi Tamiaki
Aug 2, 2008·Science·Y KashiyamaN Ohkouchi
Dec 22, 2009·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Yuki HiraiYoshitaka Saga
Mar 12, 2011·Bioorganic & Medicinal Chemistry Letters·Toru ObaHitoshi Tamiaki
Sep 6, 2018·Photosynthesis Research·Misato TeramuraHitoshi Tamiaki

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